Water → (6-Chloro-4-(methylamino)pyridin-3-yl)methanol

HRID 1430461Notes

Reaction equation

HRID 1430461 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH3:14])[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[C:11]([NH:13][CH3:14])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 20627001Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 51000240(6-Chloro-4-(methylamino)pyridin-3-yl)methanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of ethyl 6-chloro-4-(methylamino)nicotinate (4 g, 18.7 mmol) in THF (40 mL), under a N2 atmosphere, was treated portion-wise with LiAlH4 (1.4 g, 37.4 mmol), stirred for 20 min, then carefully treated with water followed by 2 N NaOH. The suspension was filtered and the filtrate was concentrated to afford (6-chloro-4-(methylamino)pyridin-3-yl)methanol (2.9 g, 91% yield), which was used in next step without purification. 1H NMR (400 MHz, DMSO-d6): δ 7.96 (s, 1H), 6.63 (s, 1H), 6.46 (s, 1H), 5.04 (s, 1H), 4.39 (m, 2H), 2.81-2.68 (m, 3H).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b76d4a05ec584215a3c8b6e105b55ff9
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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